US2887465A - Stabilization of chlorine containing polymers with (epoxyethyl) benzenes - Google Patents

Stabilization of chlorine containing polymers with (epoxyethyl) benzenes Download PDF

Info

Publication number
US2887465A
US2887465A US714079A US71407958A US2887465A US 2887465 A US2887465 A US 2887465A US 714079 A US714079 A US 714079A US 71407958 A US71407958 A US 71407958A US 2887465 A US2887465 A US 2887465A
Authority
US
United States
Prior art keywords
epoxyethyl
benzene
chlorine containing
benzenes
stabilization
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US714079A
Other languages
English (en)
Inventor
Hopff Heinrich
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
JR Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JR Geigy AG filed Critical JR Geigy AG
Application granted granted Critical
Publication of US2887465A publication Critical patent/US2887465A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/15Heterocyclic compounds having oxygen in the ring
    • C08K5/151Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515Three-membered rings

Definitions

  • epoxy compounds such as, for example phenoxy propene oxide or glycide ethers of phenols as stabilising agents for such compounds has already been suggested.
  • liquid substances are meant in which the epoxy group is bound to the aromatic nucleus by way of an oxygen atom.
  • solid polyepoxy compounds containing the epoxy group linked direct to the aromatic nucleus are excellently suitable for the stabilisation of halogen-containing macromolecular compounds, in particular polyvinyl chloride, polyvinylidene chloride, chlorinated rubber and mixed polymers containing vinyl chloride or vinylidene chloride, as well as polychlorinated diphenyls and polychloronaphthalenes.
  • polyepoxides are 1.3- or 1.4-di-(epoxyethyl) -benzene or 1.3.5-tri-(epoxyethyl)-benzene of the following formulae:
  • the new, heat stable compositions according to the present invention contain 0.1 to about 3% of the stabilisers, which amount is absolutely sulficient to attain a great improvement of the stability to heat of the products.
  • the poly- 2,887,465 Patented May 19, 1959 epoxides mentioned can also be used for the stabilising of solutions of the macromolecular halogen compounds in organic solvents.
  • Example 1 100 parts of a polymer obtained by emulsion polymerisation of vinyl chloride are mixed in powder form with 0.5 part of 1.3.5-tri-(epoxyethyl)-benzene in a ball mill. On plasticising on a hot roller mill and then pressing, sheets having excellent stability to heat are obtained.
  • Example 2 A mixed polymer from parts of vinylidene chloride and 15 parts of vinyl chloride, obtained by emulsion polymerisation is mixed with 1 part of 1.3.5-tri-(epoxyethyl) -benzene in a ball mill and then formed into bristles or little bands in an alloy extruder containing no iron. The products obtained are very light coloured and have good stability to heat.
  • Example 3 A 20% solution of chlorinated rubber which also contains 0.5% of l.4-di-(epoxyethyl)-benzene in toluene solution (calculated on the chlorinated rubber) is poured into a film. After drying, the film produced has very good stability to heat and weather.
  • Example 4 parts of an emulsion polymer of vinyl chloride are mixed with 2.5 parts of the di-epoxide from technical divinyl benzene, consisting of about 70% of the meta and 30% of the para compound, 30 parts of dioctyl phthalate are added and the whole is rolled on a heated calender into a homogeneous foil.
  • the product so obtained can be made into elastic forms which have excellent stability to heat.
  • the new heat stable composition of matter consisting essentially of a chlorine containing macromolecular com pound selected from the group consisting of polyvinyl chloride, polyvinylidene chloride and chlorinated rubber and of from 0.1 to 3%, calculated on said compound, of a solid stabiliser selected from the group consisting of 1 .3-di-( epoxyethyl) -benzene, 1.4-di-(epoxyethy1) -benzene and l.3.5-tri-(epoxyethyl)-benzene.
  • the new heat stable composition of matter consisting essentially of polyvinyl chloride and of from 0.5 to 1%, calculated on said compound, of 1.3.5-tri-(epoxyethyl) -b enzene.
  • the new heat stable composition of matter consisting essentially of polyvinylidene chloride and of from 0.5 to 1%, calculated on said compound, of 1.3.5-tri- (epoxyethyl) -benzene.
  • the new heat stable composition of matter consisting essentially of chlorinated rubber and of from 0.5 to 1%, calculated on said compound, of 1.4-di-(epoxyethy1)- benzene.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US714079A 1957-02-14 1958-02-10 Stabilization of chlorine containing polymers with (epoxyethyl) benzenes Expired - Lifetime US2887465A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH875017X 1957-02-14

Publications (1)

Publication Number Publication Date
US2887465A true US2887465A (en) 1959-05-19

Family

ID=4544323

Family Applications (1)

Application Number Title Priority Date Filing Date
US714079A Expired - Lifetime US2887465A (en) 1957-02-14 1958-02-10 Stabilization of chlorine containing polymers with (epoxyethyl) benzenes

Country Status (4)

Country Link
US (1) US2887465A (de)
CH (1) CH351749A (de)
DE (1) DE1168071B (de)
GB (1) GB875017A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3251861A (en) * 1966-05-17 Di- and triepoxtoe derivatives of trivinylcyclohexane

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101616898B1 (ko) * 2009-03-05 2016-04-29 신닛테츠 수미킨 가가쿠 가부시키가이샤 에폭시 수지 조성물

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2595619A (en) * 1948-03-04 1952-05-06 Shell Dev Use of a mixture of a diamide of a carbonic acid and an epoxy compound to stabilize a halogen containing material

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE611380C (de) * 1932-04-22 1935-03-27 I G Farbenindustrie Akt Ges Verfahren zur Stabilisierung von Chlorierungsprodukten hoehermolekularer Substanzen,insbesondere Chlorkautschuk
DE656133C (de) * 1933-12-07 1938-01-29 I G Farbenindustrie Akt Ges Verfahren zur Stabilisierung von Polyvinylchlorid
NL66626C (de) * 1946-09-26 1950-11-15

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2595619A (en) * 1948-03-04 1952-05-06 Shell Dev Use of a mixture of a diamide of a carbonic acid and an epoxy compound to stabilize a halogen containing material

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3251861A (en) * 1966-05-17 Di- and triepoxtoe derivatives of trivinylcyclohexane

Also Published As

Publication number Publication date
DE1168071B (de) 1964-04-16
GB875017A (en) 1961-08-16
CH351749A (de) 1961-01-31

Similar Documents

Publication Publication Date Title
US2564194A (en) Stabilization of high molecular weight organic material containing inorganic acid-forming elements
US2126179A (en) Light stabilization of vinyl polymers
US2887465A (en) Stabilization of chlorine containing polymers with (epoxyethyl) benzenes
US2588899A (en) Stabilized compositions containing high molecular weight halogenated materials
US2659709A (en) Stabilized vinylidene chloride compositions
US2566208A (en) Dielectric composition of halogenated aromatic hydrocarbon and organic antimony compound as a corrosion inhibitor
US2316197A (en) Polyvinyl halide composition
JPS5813094B2 (ja) 防炎性重合体組成物
GB1015028A (en) Halogenated diphenylsulphides and polymer compositions containing them
US2954363A (en) Stabilized masses of polyvinyl compounds containing halogen
US2302362A (en) Stabilization of halogen containing organic materials
GB676597A (en) Improvements in and relating to solutions of polymeric chlorotrifluoroethylene
US2627504A (en) Dielectric containing halogenated aromatic hydrocarbon and mono ortho tolyl biguanide as corrosion inhibitor
US3674695A (en) Electrical insulating compositions based on olefin polymers
US3068297A (en) Isomerization of halobiphenyls
US2174289A (en) Dielectric diluent
US2581453A (en) High-boiling esters as solvents for polychlorotrifluoroethylene
US2316481A (en) Halogenated polymers of ethylene
US3038107A (en) Liquid dielectric compositions, method of preparation and use thereof
US2136173A (en) Stable preparations of aromatic compounds containing active halogen
US2234212A (en) Polyvinyl chloride solution and method of making the same
US2578359A (en) Stabilization of halogenated organic compounds with dibutyl diphenyl tin
US2414399A (en) Stabilizer and plasticizer for vinyl resins
US2964485A (en) Color stabilization of polyvinyl alkyl ether-halogenated solvent systems with a hydrogen acceptor from the group consisting of barium ricinoleate and cadmium alpha-ethylcaproate
US2249498A (en) Coating composition